Synthesis, antimicrobial activities of novel 3-chloro-4-(2,4-difluorophenyl)-1-(3-aryl-1,8-naphthyridin-2-yl)azetidin-2-ones and 2-(2,4-difluorophenyl)-3-(3-aryl-1,8-naphthyridin-2-yl)thiazolidin-4-ones

Abstract

A novel series of 3-chloro-4-(2,4-difluorophenyl)-1-(3-aryl-1,8-naphthyridin-2-yl)azetidin-2-one 6(a–g) and 2-(2,4-difluorophenyl)-3-(3-aryl-1,8-naphthyridin-2-yl)thiazolidin-4-ones 7(a–g) were synthesized through the reaction of Schiff base 1-(2,4-difluorophenyl)-N-(3-aryl-1,8-napthridine-2-yl)methanimines 5(a–g) with chloro acetyl chloride and mercaptoacetic acid respectively. The chemical structures of the synthesized derivatives were established by ¹H-NMR, ¹³C-NMR, mass spectral, and C, H, N analysis. The synthesized compounds were evaluated for antibacterial Staphylococcus aureus, Bacillus subtilis (two Gram positive) and Escherichia coli, Klebsiella pneumonia (two Gram negative) and antifungal Aspergillus flavus, Fusarium oxysporum. The synthesized compounds showed considerable activity of antibacterial and antifungal activity comparable to that of the reference drug. The molecular docking study was succeeded to identify the likely interactions with the new synthesized derivatives 6(a–g) and 7(a–g). Docking investigation confirmed that active molecule 6b, 6d, 6f and 7b, 7d, 7f have better docking scores with protein.

Graphical Abstract

Keywords:

• Antimicrobial activities
• azetidin-2-ones
• 1,8-naphthyridine
• Schiff base
• Thiazolidin-4-ones

Acknowledgment

The authors thankfully acknowledge the Head of the Department of Chemistry, Osmania University, for providing research facilities. One of the author (KURUMANNA A) thanks the UGC, New-Delhi, India for the financial support. Directors, CFRD-OU, IICT-Hyderabad for providing spectral ¹HNMR, ¹³C NMR, and MS data.

Additional information

Funding

This work was supported by the University Grants Commission, New Delhi, India [Ref. NO: 21/12/2014(ii)EU-V].